# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19
_database_code_depnum_ccdc_archive 'CCDC 1908213'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2019-04-05 deposited with the CCDC.	2019-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H25 B O4'
_chemical_formula_sum            'C14 H25 B O4'
_chemical_formula_weight         268.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9148(5)
_cell_length_b                   9.6905(8)
_cell_length_c                   18.8528(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1628.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1197
_cell_measurement_theta_min      3.1320
_cell_measurement_theta_max      25.1880

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.681
_exptl_crystal_size_mid          0.501
_exptl_crystal_size_min          0.408
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            3866
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_max         28.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_point_group_measured_fraction_full 0.890
_reflns_number_total             2856
_reflns_number_gt                2298
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_max     0.575
_reflns_Friedel_fraction_full    0.760

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.0173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 666 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2856
_refine_ls_number_parameters     202
_refine_ls_number_restraints     142
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.5010(3) 0.3089(3) 0.15756(17) 0.0349(7) Uani 1 1 d . . . . .
O2 O 0.50828(19) 0.2353(2) 0.09581(9) 0.0405(5) Uani 1 1 d . . . . .
C3 C 0.6639(4) 0.2048(6) 0.0839(2) 0.0382(11) Uani 0.738(5) 1 d D U P A 1
C4 C 0.7448(11) 0.3177(8) 0.1273(5) 0.042(2) Uani 0.738(5) 1 d D U P A 1
C6 C 0.6905(5) 0.0596(5) 0.1125(3) 0.0629(14) Uani 0.738(5) 1 d D U P A 1
H6A H 0.795892 0.034196 0.105532 0.094 Uiso 0.738(5) 1 calc R U P A 1
H6B H 0.666681 0.057233 0.163258 0.094 Uiso 0.738(5) 1 calc R U P A 1
H6C H 0.626103 -0.005808 0.087183 0.094 Uiso 0.738(5) 1 calc R U P A 1
C7 C 0.6908(5) 0.2073(6) 0.0046(2) 0.0618(15) Uani 0.738(5) 1 d D U P A 1
H7A H 0.796465 0.186803 -0.005071 0.093 Uiso 0.738(5) 1 calc R U P A 1
H7B H 0.627311 0.137865 -0.018295 0.093 Uiso 0.738(5) 1 calc R U P A 1
H7C H 0.666016 0.298910 -0.014015 0.093 Uiso 0.738(5) 1 calc R U P A 1
C8 C 0.8894(5) 0.2729(8) 0.1619(3) 0.0664(16) Uani 0.738(5) 1 d D U P A 1
H8A H 0.963768 0.251451 0.125259 0.100 Uiso 0.738(5) 1 calc R U P A 1
H8B H 0.927314 0.347531 0.192112 0.100 Uiso 0.738(5) 1 calc R U P A 1
H8C H 0.871190 0.190682 0.190936 0.100 Uiso 0.738(5) 1 calc R U P A 1
C9 C 0.7667(7) 0.4514(5) 0.0862(3) 0.0697(16) Uani 0.738(5) 1 d D U P A 1
H9A H 0.839285 0.436376 0.047954 0.105 Uiso 0.738(5) 1 calc R U P A 1
H9B H 0.670651 0.480774 0.066013 0.105 Uiso 0.738(5) 1 calc R U P A 1
H9C H 0.804386 0.523018 0.118310 0.105 Uiso 0.738(5) 1 calc R U P A 1
C3' C 0.6686(17) 0.2567(15) 0.0656(7) 0.041(4) Uiso 0.262(5) 1 d D U P A 2
C4' C 0.756(3) 0.313(2) 0.1306(14) 0.041(5) Uiso 0.262(5) 1 d D U P A 2
C6' C 0.7171(18) 0.1151(15) 0.0405(9) 0.072(4) Uiso 0.262(5) 1 d D U P A 2
H6D H 0.722244 0.051998 0.081021 0.108 Uiso 0.262(5) 1 calc R U P A 2
H6E H 0.644425 0.079980 0.005890 0.108 Uiso 0.262(5) 1 calc R U P A 2
H6F H 0.816198 0.121597 0.018156 0.108 Uiso 0.262(5) 1 calc R U P A 2
C7' C 0.6607(14) 0.3537(15) 0.0033(6) 0.058(4) Uiso 0.262(5) 1 d D U P A 2
H7D H 0.629261 0.445248 0.019664 0.088 Uiso 0.262(5) 1 calc R U P A 2
H7E H 0.759723 0.360291 -0.018974 0.088 Uiso 0.262(5) 1 calc R U P A 2
H7F H 0.587950 0.318674 -0.031240 0.088 Uiso 0.262(5) 1 calc R U P A 2
C8' C 0.854(2) 0.2079(19) 0.1676(9) 0.067(5) Uiso 0.262(5) 1 d D U P A 2
H8D H 0.935616 0.179857 0.135704 0.101 Uiso 0.262(5) 1 calc R U P A 2
H8E H 0.897036 0.249182 0.210557 0.101 Uiso 0.262(5) 1 calc R U P A 2
H8F H 0.794361 0.126997 0.180490 0.101 Uiso 0.262(5) 1 calc R U P A 2
C9' C 0.8475(17) 0.4442(15) 0.1186(8) 0.061(4) Uiso 0.262(5) 1 d D U P A 2
H9D H 0.927985 0.425467 0.084564 0.092 Uiso 0.262(5) 1 calc R U P A 2
H9E H 0.781983 0.516817 0.099877 0.092 Uiso 0.262(5) 1 calc R U P A 2
H9F H 0.891064 0.474594 0.163704 0.092 Uiso 0.262(5) 1 calc R U P A 2
O5 O 0.63646(19) 0.3489(2) 0.18259(10) 0.0461(6) Uani 1 1 d . . . . .
C10 C 0.3524(3) 0.3221(3) 0.20208(14) 0.0359(7) Uani 1 1 d . . . . .
C11 C 0.2628(3) 0.4310(3) 0.19715(14) 0.0362(6) Uani 1 1 d . . . . .
H11A H 0.175230 0.435937 0.225738 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2978(3) 0.5441(3) 0.14789(15) 0.0376(6) Uani 1 1 d . . . . .
O12 O 0.4065(2) 0.5445(2) 0.10931(11) 0.0515(6) Uani 1 1 d . . . . .
O13 O 0.1941(2) 0.6437(2) 0.15065(10) 0.0446(5) Uani 1 1 d . . . . .
C14 C 0.2034(4) 0.7671(3) 0.10509(16) 0.0492(8) Uani 1 1 d . . . . .
C15 C 0.0666(4) 0.8496(4) 0.1271(2) 0.0778(13) Uani 1 1 d . . . . .
H15A H -0.023482 0.792749 0.121539 0.117 Uiso 1 1 calc R U . . .
H15B H 0.058207 0.931925 0.097130 0.117 Uiso 1 1 calc R U . . .
H15C H 0.076797 0.877603 0.176808 0.117 Uiso 1 1 calc R U . . .
C16 C 0.1905(5) 0.7225(4) 0.02780(16) 0.0705(11) Uani 1 1 d . . . . .
H16A H 0.281191 0.672082 0.013986 0.106 Uiso 1 1 calc R U . . .
H16B H 0.179231 0.804228 -0.002364 0.106 Uiso 1 1 calc R U . . .
H16C H 0.102795 0.662572 0.022080 0.106 Uiso 1 1 calc R U . . .
C17 C 0.3443(4) 0.8459(4) 0.12061(18) 0.0607(10) Uani 1 1 d . . . . .
H17A H 0.353131 0.860462 0.171881 0.091 Uiso 1 1 calc R U . . .
H17B H 0.340724 0.935444 0.096477 0.091 Uiso 1 1 calc R U . . .
H17C H 0.431074 0.793420 0.103619 0.091 Uiso 1 1 calc R U . . .
C18 C 0.3166(4) 0.2034(3) 0.25111(17) 0.0523(8) Uani 1 1 d . . . . .
H18A H 0.397451 0.192997 0.285931 0.078 Uiso 1 1 calc R U . . .
H18B H 0.307130 0.118287 0.223427 0.078 Uiso 1 1 calc R U . . .
H18C H 0.222023 0.221984 0.275819 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O5 1.353(4) . ?
B1 O2 1.367(4) . ?
B1 C10 1.573(4) . ?
O2 C3 1.436(4) . ?
O2 C3' 1.552(16) . ?
C3 C7 1.514(6) . ?
C3 C6 1.525(7) . ?
C3 C4 1.545(7) . ?
C4 O5 1.453(12) . ?
C4 C8 1.509(8) . ?
C4 C9 1.522(8) . ?
C3' C7' 1.506(15) . ?
C3' C6' 1.515(17) . ?
C3' C4' 1.549(17) . ?
C4' O5 1.49(4) . ?
C4' C8' 1.512(19) . ?
C4' C9' 1.53(2) . ?
C10 C11 1.327(4) . ?
C10 C18 1.509(4) . ?
C11 C12 1.470(4) . ?
C12 O12 1.212(3) . ?
C12 O13 1.338(3) . ?
O13 C14 1.475(3) . ?
C14 C17 1.499(4) . ?
C14 C15 1.516(4) . ?
C14 C16 1.524(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 B1 O2 113.8(2) . . ?
O5 B1 C10 122.8(2) . . ?
O2 B1 C10 122.5(3) . . ?
B1 O2 C3 106.6(2) . . ?
B1 O2 C3' 106.6(5) . . ?
O2 C3 C7 107.7(4) . . ?
O2 C3 C6 106.5(4) . . ?
C7 C3 C6 109.8(4) . . ?
O2 C3 C4 102.9(5) . . ?
C7 C3 C4 116.0(6) . . ?
C6 C3 C4 113.2(5) . . ?
O5 C4 C8 108.5(6) . . ?
O5 C4 C9 105.8(6) . . ?
C8 C4 C9 110.8(6) . . ?
O5 C4 C3 102.5(6) . . ?
C8 C4 C3 115.1(7) . . ?
C9 C4 C3 113.2(6) . . ?
C7' C3' C6' 109.5(12) . . ?
C7' C3' C4' 115.0(13) . . ?
C6' C3' C4' 114.9(15) . . ?
C7' C3' O2 109.0(10) . . ?
C6' C3' O2 104.9(11) . . ?
C4' C3' O2 102.6(15) . . ?
O5 C4' C8' 105.7(18) . . ?
O5 C4' C9' 106.3(16) . . ?
C8' C4' C9' 108.4(18) . . ?
O5 C4' C3' 104.2(17) . . ?
C8' C4' C3' 115.0(16) . . ?
C9' C4' C3' 116.2(17) . . ?
B1 O5 C4 106.5(3) . . ?
B1 O5 C4' 109.9(7) . . ?
C11 C10 C18 121.4(2) . . ?
C11 C10 B1 122.3(3) . . ?
C18 C10 B1 116.3(2) . . ?
C10 C11 C12 120.6(2) . . ?
O12 C12 O13 125.0(3) . . ?
O12 C12 C11 123.5(3) . . ?
O13 C12 C11 111.5(2) . . ?
C12 O13 C14 121.6(2) . . ?
O13 C14 C17 110.3(2) . . ?
O13 C14 C15 102.9(2) . . ?
C17 C14 C15 110.6(3) . . ?
O13 C14 C16 108.8(3) . . ?
C17 C14 C16 113.2(3) . . ?
C15 C14 C16 110.5(3) . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.036

